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- Herausgeber: John Wiley & Sons
- Kategorie: Ratgeber
- Sprache: Englisch
Build a new life and career while shaping our digital future with NFTs and blockchain technology
In Digital Mavericks: A Guide to Web3, NFTs, and Becoming the Main Character in the Next Internet Revolution, founder, NFT collector, and tech entrepreneur Debbie Soon delivers an exciting and eye-opening exploration of the seismic changes and tremendous opportunities that can be found at the intersection of creativity and technology. You’ll learn about how blockchain technology and non-fungible tokens (NFTs) are challenging the way we think about our careers and discover inspirational stories behind the personal triumphs and challenges experienced by successful artists, entrepreneurs, and technologists.
This book is a career guide for the new age of the Internet, a world being reshaped by blockchain technology. Despite the countless fortunes Web3 has already created, it remains a space subject to both criticism and skepticism. Digital Mavericks is an easy-to-follow roadmap for those eager to play a part in shaping the future of our increasingly digital world. You’ll also find:
- In-depth interviews and stories from movers and shakers in the space such as entrepreneur Randi Zuckerberg, digital art collector Cozomo de Medici, AI artist Claire Silver, technologist Jesse Pollak, and many more.
- An explanation of the evolution of the Internet, the basics of how Web3 works and is being used today, and its historical significance at this moment in time.
- A step-by-step guide on how best to enter and navigate the Web3 space, from understanding and transferring your skillset to finding your community and staying level-headed through the noise.
- Predictions for the future and how we can best prepare ourselves for the impact of regulatory changes and generative AI on blockchain adoption.
An inspiring and insightful take on the Wild West of Web3, Digital Mavericks will prove invaluable for anyone interested in understanding the biggest technological revolution of our generation and how we can all work together in transforming the way we interact, transact, and collaborate with one another.
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Veröffentlichungsjahr: 2025
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Table of Contents
Cover
Table of Contents
Title Page
Copyright
Dedication
Introduction
Notes
PART 1: Viva la Revolución
1 Growing Up with the Internet
Notes
2 Taking Back Control
Note
3 Of Sliced Bread and Paper
First Off, Paper Is Awesome
NFTs Are Just Magical Pieces of Digital Paper
The Magic NFTs Run On Is the Blockchain
We Use Magic Money Called Cryptocurrencies to Operate on the Blockchain
Cryptocurrencies Can Be Used to Buy NFTs, Which Can Be Tied to Almost Anything
Notes
PART 2: How to Become a Maverick
4 Step 1: Identify Your Glow Stick Moment
Notes
5 Step 2: Understand and Hold On to Your Why
Notes
6 Step 3: Get Your Hands Dirty
#1: Get Social
#2: Do the Deed
#3: Safety First
Notes
7 Step 4: Transfer Your Skills
Notes
8 Step 5: Join a Cabal … or Make Your Own
Notes
9 Step 6: Embrace the Chaos
Notes
10 Step 7: Craft and Commit to a Ritual
#1: Nurture
#2: Educate
#3: Connect
Notes
PART 3: A New Era
11 The Robots Are Coming
Notes
12 A Promised Land of False Starts
Notes
13 Diversity, Equity, and the Inclusiverse
Notes
Conclusion
Note
Glossary
Resources
Introduction
Part 1
Chapter 2
Chapter 3
Meet a Maverick: Jesse Pollak
Part 2
Chapter 8
Meet a Maverick: Zeneca
Meet a Maverick: Cozomo de' Medici
Chapter 10
Meet a Maverick: Micah Johnson
Part 3
Chapter 11
Meet a Maverick: Claire Silver
Chapter 12
Chapter 13
Meet a Maverick: Larisa Barbu
Conclusion
Acknowledgments
About the Author
Index
End User License Agreement
List of Illustrations
Introduction
Figure 1 Marina Bay Sands.
Figure 2 My very first NFT.
Chapter 2
Figure 2.1 “Internet ‘may be just a passing fad'” from the Daily Mail, Decem...
Figure 2.2 One of Foodmasku's artworks.
Chapter 3
Figure 3.1 The United States Constitution.
Figure 3.2 Example of a spatial intelligence test question.
Figure 3.3 Collectible Avatars on sale on Reddit.
Chapter 4
Figure 4.1 Collage art I made from magazines as a teenager.
Chapter 6
Figure 6.1 One of Shavonne Wong's 3D artworks from her Love is Love collecti...
Chapter 7
Figure 7.1
All Our Faces #2
by Jimena Buena Vida.
Chapter 8
Figures 8.1
Empaths
by Adamtastic.
Figure 8.3 ZenAcademy Genesis membership token.
Chapter 9
Figure 9.1 Checks VV by Jack Butcher.
Figure 9.2 NFT Money Flow adapted from BatSoupYum's original diagram in Augu...
Figure 9.3 Right‐click and Save As Guy by XCOPY, which resides in The Medici...
Chapter 11
Figure 11.1 One of the pieces from Claire Silver's corpo | real collection. ...
Guide
Cover
Table of Contents
Title Page
Copyright
Dedication
Introduction
Begin Reading
Conclusion
Glossary
Resources
Acknowledgments
About the Author
Index
End User License Agreement
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DIGITAL MAVERICKS
A GUIDE TO WEB3, NFTs, AND BECOMING THE MAIN CHARACTER OF THE NEXT INTERNET REVOLUTION
DEBBIE SOON
Copyright © 2025 by John Wiley & Sons, Inc. All rights reserved, including rights for text and data mining and training of artificial technologies or similar technologies.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.Published simultaneously in Canada.
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Library of Congress Cataloging‐in‐Publication Data
Names: Soon, Debbie (Businesswoman), author.Title: Digital mavericks : a guide to Web3, NFTs, and becoming the main character of the next Internet revolution / Debbie Soon.Description: Hoboken, New Jersey : Wiley, [2025] | Includes bibliographical references and index.Identifiers: LCCN 2024028327 (print) | LCCN 2024028328 (ebook) | ISBN 9781394220892 (hardback) | ISBN 9781394220908 (adobe pdf) | ISBN 9781394233342 (epub)Subjects: LCSH: NFTs (Tokens) | Blockchains (Databases) | Art and technology.Classification: LCC HG1710.3 .S66 2025 (print) | LCC HG1710.3 (ebook) | DDC 332.4/048–dc23/eng/20240719LC record available at https://lccn.loc.gov/2024028327LC ebook record available at https://lccn.loc.gov/2024028328
Cover Design: WileyCover Image: © Jamaali Roberts
To the dreamers who dare to do, and the doers who dare to dream:
This is our time.
Introduction
It is the year 2018. The movie Crazy Rich Asians is released, becoming the most successful studio romantic comedy in nearly a decade at the US box office. Asians all over the world rejoice – after all, this is the first movie with an all‐Asian cast coming out of Hollywood since 1993, and what a successful one at that.
For me, the movie quite literally hit home. Set in Singapore, Crazy Rich Asians was the first thing in the then‐30 years of my life that gave the world a frame of reference for what it was like to live and grow up there. As heavily glamorized as the movie was, the picture it painted of Singapore was an undeniable improvement over what many others had until then assumed to be “some part of China.”
The Singapore the world knows today resembles little of what I remember growing up in the ’80s. Many landmarks that adorn our postcards (do people still send those anymore?) or tourism commercials were built in the last 10–15 years. In fact, I distinctly remember coming back for summer break while studying in college abroad, only to be completely taken aback by what looked like a spaceship perched precariously across three towering buildings. That architectural wonder turned out to be a Vegas‐style integrated resort called Marina Bay Sands, and consisted of a casino, hotel, and shopping mall. It would later become a defining part of the city's skyline in years to come, with many of us forgetting that even the land it sits on was a result of man‐made intervention (Figure 1).
Yet, as modern and technologically advanced Singapore appears to be, it still upholds socially conservative values, where free speech is considered a Western ideal and privilege that one chooses to pursue at their own peril. Locals are deterred from patronizing the aforementioned casino by being charged an entry levy, while the Singapore government has just started wrapping its head around the decriminalization of gay sex (same‐sex marriage remains very much prohibited).
Figure 1Marina Bay Sands.
Source: Hu Chen/UnSplash
I speak about Singapore so much partly because it has shaped so much of who I am – I was born and raised, and have established most of my career here, despite having since moved to Los Angeles after a pandemic‐inspired move. But also because Singapore, a city‐state of just 280 square miles with zero natural resources and a mere 59 years of history, epitomizes the spell‐binding tension that has stemmed from a constant need to progress and innovate itself out of irrelevance.
Whether we know it yet, we as humans are in the crosshairs of a similar tension. In fact, we may very well be at the juncture of having to reinvent ourselves out of oblivion. The continued advances of blockchain1 technology and now artificial intelligence (AI) represents a real threat that could easily render our place in the workforce, and by extension society, vulnerable. Yet, only a few of us are willing to confront that inevitability, let alone reflect upon our roles in that new reality – be that in the next 1, 5, or 10 years.
Those of us who do are what I like to refer to as mavericks – and more precisely, digital mavericks.
Taking risks, breaking the rules, and being a maverick have always been important but today they are more crucial than ever.
– Gary Hamel, American management consultant
Today, I consider myself very much in the good company of fellow digital mavericks. Despite buying my first cryptocurrency2 in the spring of 2019, it wasn't till the end of 2021 that I started getting intrigued about Web3 (a term used to describe a new evolution of the Internet powered by blockchain technology), and in particular non‐fungible tokens3 (NFTs). This was considered late by many – I wasn't an early collector of CryptoPunks or Bored Ape Yacht Club, nor did I really care to be. I was just intrigued by what I saw as an undeniable movement toward the purchasing, consuming, and owning of digital goods. After reading a New York Magazine article published in November 2021 titled “A Normie's Guide to Becoming a Crypto Person,”4 I decided to get my feet wet by resurrecting my presence on X (formerly known as Twitter, and where the last tweet I had posted was probably in 2012), since that was where all the “crypto people” resided online.
According to the New York Magazine article, it was uncool to use my real name or my real photo on Twitter. I found and purchased an NFT of an avatar I liked – a witchy character with a crescent‐shaped talisman and covetable long flowing black hair from an NFT collection called Crypto Coven. I also adopted the user handle safronova (Figure 2).
Safronova is actually the last name of a Russian volleyball player that I had seen once on TV during the 2004 Summer Olympics – liking how it sounded (it's a few letters away from the word supernova, which I was particularly fond of due to the song “Champagne Supernova” by British rock band Oasis), I ended up using it as a gaming handle in my teenage years. While I had not gamed for a while, it felt befitting to bring it back as a pseudonym in an environment where it seemed many assumed alternate identities.
Figure 2My very first NFT.
From there, I started to pen Twitter threads, sharing my learnings and takeaways about Web3, while also joining communities housed in Discord servers and making new friends over the Internet. It was in Discord that I met my now cofounder Randi Zuckerberg (as my witchy Internet self), the creator of Facebook Live as well as multiple‐time Tony Award–winning Broadway producer – more on that later.
Together, we are building a company called HUG, a social platform for a new generation of blockchain‐curious artists to showcase and sell their work (both on and off the blockchain), while connecting with each other and one‐of‐a‐kind opportunities. Today, we are home to tens of thousands of artists across more than 160 different countries.
Through HUG, I am fortunate to work and interact with artists daily. Not only am I surrounded and inspired by creativity every single day, but I also get to see and experience firsthand how blockchain technology is evolving and creating new opportunities for these creators turned creative entrepreneurs.
Building on the front lines of Web3 is both empowering and lonely. There are days when it feels as if I am leading the charge in a revolution against Big Tech, seizing back control for the proletariat of everyday creators through the promise of true ownership. Most days, not only does the road ahead feel like June Gloom5 in LA – most of the people in my personal life and even those I am advocating for (i.e. artists who have not yet dived into the world of NFTs) have little idea of what I do. “What the heck is an NFT anyway?” they say. “Isn't crypto just full of scammers?”
Like many other books written about Web3, Digital Mavericks is a time capsule, simply because of how much this space is about to evolve. That said, this is also an intentional snapshot of all the risk‐takers who are making history as we speak.
There's a saying widely attributed to Winston Churchill that goes, “History is written by the victors.” In my mind, that has never been a fair representation of what history is or should be (Mr. Miles, my high school history teacher, will be proud). Moreover, this characterization feels exceedingly unfair for something like Web3 – a technology, but more importantly a movement that is so deeply rooted in and driven by community. In fact, years down the road, my wish is for us to come out the other end fixated less on who's won and who's lost, but more so on what we have learned and on the change that we have fought for and inspired.
By the end of this book, I hope that you will have a deeper understanding of what Web3 is, why you should care, and why there are so many of us here breaking rules and challenging the status quo. More importantly, I also hope to convince you that you too have a place in this revolution if you choose to participate.
Do not get me wrong – Web3 is not perfect, be it the technology, the culture, how it is branded, and more. What I do know is that we are still early, yes – even in 2024, despite the first cryptocurrency (Bitcoin!) being created in 2009 and the first NFT being minted6 (meaning, to be created on the blockchain) in 2014. I do not know about you, but I believe that anytime you are early to something is an opportunity to choose the role you would like to play, as well as shape the experience you'd like to have within it.
There is an equally high probability that after reading this you may think that Web3 and everything it entails (blockchain technology, crypto, NFTs, etc.) is not for you. You may even decide that you want nothing to do with it (even though my personal belief is that it will become ingrained in our lives without us realizing it). That's okay too.
Digital Mavericks is also meant to be an anthology – a collection of stories about everyday people like myself who have discovered a new sense of purpose and calling since encountering Web3. And while the whole idea of being on the cutting edge of emerging tech has been a huge part of that, I think you will realize that the one thing that has got us to this (at times cult‐like) sense of wonder is the magical human connections we never thought possible.
Disclaimer: This book is anything but technical. In fact, I deliberately made it as nontechnical as possible. Not only are there far more qualified scholars on the subject of blockchain technology than me, but I also wanted this book to ultimately be approachable and to inspire further thought and action in even the most skeptical and unacquainted of readers.
To help you understand this new digital frontier, this book is split into three parts. The first, Viva la Revolución, is an introduction to what this Internet revolution even is. It provides history and context to how the Internet came to be, which if you are a millennial like me, will be like a trip down memory lane, before introducing you to Web3 through what are hopefully familiar concepts.
The second, How to Become a Maverick, is a step‐by‐step guide to how you can start to immerse yourself in this onchain world. Whether you are looking to eventually build a career here or are simply looking to become a more involved industry participant, here are my tips and tricks to help you stay grounded, survive the noise, and eventually thrive and find your true purpose.
The third and final part, A New Era, runs you through a few predictive trends I feel are worth highlighting and bracing yourself for. Because this space moves so fast, it is near impossible to make accurate forecasts of what will happen, and when. Nonetheless, I hope that these discussions will help you stay alert, and more importantly, get you excited about the role that you can play in shaping our digital future.
Along the way, you will also be introduced to several digital mavericks I've come to know and love. Some of them are artists, some are founders just like myself, others are community members and builders. While you may think every one of them crazy, you will notice that before Web3, the lives they led were nothing but relatable and dare I say it, normal. I hope that through their stories, you will be encouraged to take on risks of your own – to learn more and be curious about an industry that seems so incredibly foreign; to seek a career that aligns with your values and passions; and last but not least, to be open to picking up new skills in the advent of all the change that is about to confront us.
You see, Web3 should not be something that just happens to us. Instead, it should be a level playing field in which we get to take control of our own narrative, where we let our wants and needs determine what needs to be built, and how.
Welcome to Digital Mavericks, where the main character of the biggest Internet revolution our generation is about to see is none other than you.
Notes
1.
The blockchain is essentially a digital ledger (i.e. book of accounts) of transactions that is stored on multiple computers in a network, making the ledger decentralized and a secure way to record and verify information.
2.
Cryptocurrency refers essentially to digital money that does not depend on a bank or financial institution to verify transactions made with it. Instead, transactions are verified and recorded on the blockchain, a decentralized ledger.
3.
Non‐fungible tokens (NFTs) are created and recorded on the blockchain similar to cryptocurrencies, but unlike the latter, are unique and not interchangeable, which is why they are referred to as non‐fungible.
4.
A normie is defined as someone who is new to or uninvolved in the world of cryptocurrency. The
New York Magazine
article goes further as to identify a normie as “a skeptic who has stayed out of the crypto market, either from sheer bewilderment or the suspicion that it is a giant pyramid scheme.”
5.
June Gloom is a term used to describe the weather phenomenon of cloudy, overcast skies during the late spring and early summer months in Southern California.
6.
Minting refers to the process of creating a non‐fungible token on the blockchain.
PART 1Viva la Revolución
You cannot buy the revolution. You cannot make the revolution. You can only be the revolution. It is in your spirit, or it is nowhere.
– Ursula K. Le Guin, American author
1Growing Up with the Internet
I WAS BORN in 1988, putting me squarely in the middle of the generation we now term millennials. Millennials were the first generation to grow up with the Internet and then social media. It wasn't till years later that I realized this transition from my childhood into young adulthood also mirrored the evolution of the different phases of the Internet – and what we now term going from Web1 to Web2.
Web1 represents the early read‐only version of the Internet. Back then, most people were passive consumers of information made available online. Website pages were static and gave users little way to interact with them. From a slightly more technical standpoint, content on website pages in Web1 were also hosted on the server's file system, as opposed to a relational database management system (RDBMS), which allows users to store, sort, and query information more easily.
Web1 was basically like taking a real‐world dictionary, digitizing it, and making its content available for everyone to look at (but not react to) it online. From a timestamp perspective, I will also always associate Web1 with dial‐up Internet, which in itself is embodied by a harrowing sound of nostalgia. More accurately, the cacophony of beeps and tones, which usually lasted around 19 seconds, was how long it took for us to access the World Wide Web.
Getting online was a scarce and prized event in my household growing up. Not only were Internet speeds painfully slow – it took around 20–30 minutes to download my favorite song by Christina Aguilera (“Genie in a Bottle,” 1999) just so I could listen to it on demand and on repeat – but with the modem being connected to the phone lines, it also meant that anytime someone was connected to the Internet, our entire family would be incommunicado. Such was life before the dawn of mobile phones.
Yet, Web1 itself felt enticing enough at the time. Through a now‐defunct MSN Messenger, we all got to talk to our newly met classmates and fifth‐grade crushes, and then reinforce any budding friendships by recanting prior night conversations in class. Homework assignments felt easier too – asking Jeeves was a far quicker way of getting information than trying to navigate the Dewey decimal system in our school libraries.
Believe it or not, Web1 was the Internet I was familiar with all the way through graduating from high school. That said, as with anything, the move from Web1 to Web2 did not happen overnight, nor was it a result of a single discrete occurrence. In my teenage years, many of my peers and I dabbled in writing and putting out personal content on the Internet. We set up Livejournals and Tumblrs to share our teenage angst with strangers from across the world. It was exciting, nerve‐racking, but also liberating. Those of us who were more adventurous went on to build personal websites on Geocities, before graduating to buying our very first domain names.
Then came Web2. Putting content and a little bit of ourselves into the world was now easier than ever. For me, the dawn of Web2 could not have come at a better time. I had just graduated from high school in the year 2006 and was presented with a life‐changing opportunity to pursue a college education abroad through a scholarship from the Singapore government. I could not have been happier.
While I was filled with excitement about what this new chapter was about to bring (Independence! Freedom! New experiences!), it is never easy leaving friends, family, and everything you had ever known in life behind. Thankfully, the year 2006 also coincided with the year Facebook was made available to the general public. There was now an easy and what felt like a natural way to keep in touch with people from back home.
As I would soon come to learn, Facebook also made forming new friendships slightly easier in what would be a deeply unfamiliar and uncomfortable cultural environment (yes, the move from Singapore to the UK as an 18‐year‐old was not quite as easy as I thought it would be). Web2 gave rise to social networking, allowing us to build and maintain friendships with people from all around the world, while also facilitating the forming of digital communities based on shared interests and values.
The continued development of Web2, if we can even call it that, was simply an extension of the different ways in which humans connect and communicate. We went from text (Twitter) to photos (Instagram) to videos (YouTube, TikTok), where everyone could become a content creator in the medium they felt most comfortable. Those who were the earliest in embracing what Web2 could offer have gone on to become highly successful full‐time content creators (or some may say, influencers), a career path which up until 15 years ago would have seemed completely made up.
Because the astronomic rise and penetration of Web2 occurred while I was in college, I never thought twice about what its significance was, let alone the role I could or should play in it. Not only was I studying for a degree in economics and hence more preoccupied with the implications of the global financial crisis, but I was also trying to figure out how to regulate my Asian flush so I could better fit in in a country with a heavy drinking culture.
Before I knew it, I, like many others, became just one of many passive users of the Web2 Internet. I mindlessly consume and react to the content that miraculously appears on my feed, I buy one too many things I do not need from the ads that I am served and in doing so, keep the wheels of the algorithm turning so it can keep doing what it does better.
Herein lies the pitfalls of Web2. While Web2 has delivered significant benefits to humankind, be it connecting long‐lost friends or surfacing information we are seeking more quickly, it has done so at a price. “If you are not paying for the product, you are the product” is one of the most repeated quotes from Netflix documentary The Social Dilemma. Indeed, Web2 platforms have been able to become the most powerful advertisers the world has ever seen, by utilizing and selling the data and personal information we have so readily shared with them.
In the Internet revolution from Web1 to Web2, many of us have unwittingly played the role of what is now commonly known as a non‐player character (NPC).1 Compared to the early days of Web1, which was a new and novel way for everyday people to discover information and have fun, Web2 has to some extent taken that agency away by turning every single one of those activities into monetizable events.
Today, we are right at the cusp of another Internet revolution – from Web2 to Web3. And just like the previous revolution, this is a defining moment that will change how we interact, communicate, and collaborate, not just with each other but with brands, corporate entities, and even governments.
But Web3 is not just a technological innovation built on the backs of blockchain technology. It is also a cultural movement, in which many proponents and early builders in Web3 are viewing it as an opportunity to right the wrongs of Web2. After all, if Web2 companies are monetizing off the data and content that all of us have created, should we not also have the opportunity to monetarily benefit from what is fundamentally ours?
If Web1 was read‐only, and Web2 is read and write, Web3 is a depiction of the Internet where we are able to read, write, and own our content. Web3 is about us, the everyday content creators, taking back control of what has been ours all along.
***
MEET A MAVERICK: How Randi Zuckerberg Is Setting Personal Records in the Race from Web2 to Web3
Randi Zuckerberg's unique background puts her at the forefront of both technology and media. As an early employee at Facebook and the creator of Facebook Live, she was on the front lines of shaping how billions of people consume content. Today, Randi is the founder and CEO of HUG, a social marketplace for next‐generation creators to showcase and sell both onchain2 and offchain3 work. Randi is also an accomplished artist and producer who has performed on Broadway, won three Tony Awards, and hosts a weekly business talk radio show, Randi Zuckerberg Means Business on SiriusXM.
In April of 2024, Randi Zuckerberg had just competed in two out of six of the World Marathon Majors less than one week apart just a few weeks after recovering from a partially torn hamstring. She even achieved her second ever fastest marathon time of 3 hours, 37 minutes, and 5 seconds at the latter race at the London Marathon. Yet, the very next day, it was a different Zuckerberg that had made the headlines of Runner's World magazine.
While many of us may have experienced living in constant comparison to a family member (myself included), few will be able to understand what it's truly like when the family member in question is not only a household name but someone whose life's work has intimately transformed the way the entire world interacts with each other. In fact, as one of four children to a dentist father whose practice was located at the first floor of their house, Randi's childhood seemed remarkably normal aside from waking up regularly to the sounds of dental drills. “All four of us are pretty close in age, but we are such wildly different humans,” Randi says about her siblings. “I was a drama nerd, Mark was into computers, and my two younger sisters were both really academic and sporty respectively … we were basically the Spice Girls if they were a family!”
For the longest time, musical theater was all Randi wanted to do. From the time she got gifted a Fisher Price record player at age two, Randi started singing and dancing to whomever would grant her an audience, and it would not take long before she started to more seriously rehearse and audition for performances at school. No matter how small the stage was at the time, performing imparted some valuable life lessons to Randi early on. She recalls a time when her mother made her demand for a solo at a choral recital in sixth grade even though no one had received one. “My mom was picking me up after practice and told me she would not move the car until I had gone back to ask for a solo,” Randi says. “I was filled with so much anxiety, and even though it was so horrifically awkward, I asked my choir director Mr. Burke anyway.” Randi ended up getting her first ever solo performance, and even though it was not more than 30 seconds, it taught her something she still believes in till today: if you do not ask for what you want, the answer will always be no.
Throughout high school, Randi continued to take her musical theater career aspirations seriously. She trained with an opera company and even got accepted into Juilliard, one of the world's most prestigious performing arts schools, whose alumni have won hundreds of any award you could think of from the Pulitzer Prize to the Oscars. Having also been accepted into Harvard and being faced with the decision of which school to attend, it was at this time when Randi first got served with a huge reality check from her music teacher. “He sat me down seriously and told me that I was not quite talented enough, and if I had a chance to go to Harvard, I should do that instead,” Randi recalls. While that conversation hurt, it also felt surprisingly liberating. “I kind of already knew that I had hit a ceiling with what I could do in terms of pure talent,” Randi says. “In some ways I felt relieved that I was now free to pursue other things.”
It wasn't immediately clear to Randi what those other things were. “When you are a little girl, you often hear that you can have any job you want … as if it was something you could pick from a list of jobs that already existed,” Randi tells me. “What no one ever tells you is that with entrepreneurship, you can actually create any job you want.” Still, it would take a few years before Randi were to experience that possibility for herself. Instead, she fell in love with psychology classes at Harvard, where her classmates included renowned organizational psychologist Adam Grant and Oscar‐winning actress Natalie Portman, and started to take an interest in business and marketing. “I got really intrigued by nature versus nurture and the emerging fields of positive and emotional psychology,” Randi says. “Marketing felt like a way to apply these theories of why people do the things that they do in the real world.”
Randi's first job out of college was in the Digital Marketing department of Ogilvy & Mather, a global advertising and brand agency. At the time though, that department felt more like a start‐up housed within a large company. “I was actually pretty disappointed when I got staffed in that department,” Randi laughs. “Especially when my other friends at Ogilvy were all working on glamorous television campaigns.” Within a year, not only did Digital Marketing at Ogilvy end up becoming the company's most successful and fastest‐growing team, but it also became the reason for a bunch of text messages she started to receive from her brother, Mark.
“My brother reached out to say, hey, I have this little start‐up and could really use some advice from someone who understands digital marketing,” Randi recalls. What was meant to be a brief consultation and weekend visit to Silicon Valley quickly turned into Randi negotiating a full‐time offer to join her brother at Facebook. “Facebook was just a tiny office in Palo Alto with less than twenty people,” Randi says. “Even then, I could tell that this small team truly believed that they were going to change the world and the way that we all communicated. They were working eighteen‐hour days and yet seemed so happy.”
What Randi saw was entrepreneurship in action. It quickly dawned upon her that by joining a start‐up, she could be making strategic decisions at age 24 that shaped a company's trajectory, versus having to wait over 10 years in corporate America just to be let into the boardroom. “I was excited about the product and mission at Facebook, but I also saw it as a way for me to bypass a decade of my career,” Randi says. Indeed, when Facebook started to field potential television and movie deals such as the 2010 film The Social Network, it came down to Randi to run the company's entire media operations. “Prior to joining Facebook, I had spent some time working on a TV series called Forbes on Fox,” Randi tells me. “And because I was the only person in the company that had ever stepped onto a television set, I was asked to run that entire part of the business.”
While at Facebook, Randi continued to work across several large projects, but perhaps none as influential as her work with Facebook Live. “When the iPhone first came out, I started to get really interested in the possibility of mobile live streaming,” Randi recalls. “It wasn't even called live streaming at the time, but all I could think about was how we could each be our own media company if we were all holding something in the palm of our hands that had the computing power of a spaceship.”4 Initially conceived from a company hackathon, Facebook Live took years before becoming a commercially viable reality – its early iterations required large backpacks of equipment to simply be able to capture and then transmit live footage. Once it did however, it became home to not just celebrities such as Oprah Winfrey but also political figures such as President Obama. Randi ended up being nominated for an Emmy for Facebook's live coverage of the midterm elections in 2010.
While to onlookers it may have seemed that there could be no slowing Facebook down, it wasn't always a bed of roses. “The invention of the iPhone really freaked a lot of people out,” Randi says. “In a few months, we went from 90% of our users using Facebook on a desktop to almost everyone switching their usage to mobile. None of our engineers had any experience with mobile, let alone the iPhone, since everything up until that point had been created from within Apple.” Not knowing whether the iPhone and iOS were simply a fad or here to stay, Facebook made the decision to embrace the Apple ecosystem and train their engineers on it. “Betting on the iPhone turned out to be the right bet, but what if it had not worked out? We basically bet our entire company on it,” Randi added.
Seven years into her career at Facebook, Randi eventually decided to take a different bet of her own, embracing motherhood and starting a family with her husband, Brent. “I was very pregnant during the Facebook Live broadcast with President Obama,” Randi laughs. “We were also scheduled to do a Facebook Live with Hugh Jackman, whom I was absolutely obsessed with, when my water broke.” Randi got rushed to the hospital to deliver her first son, Asher, and till today, has yet to meet the actor most famously known for playing Wolverine in the X‐Men movies.
Cliché as it may sound, going on maternity leave and taking some time away from Facebook gave Randi an opportunity to properly examine where she was at in life. “Facebook had been such an incredible journey, and I had absolutely zero regrets about that experience,” Randi says. “But I also realized I had spent almost an entire decade in service of someone else's dream as a supporting character.” Ready for a leading lady role, Randi eventually stepped away from Facebook, opting instead to found her own production company, where she worked on a number of projects with varying degrees of success. While her first book with HarperCollins, Dot Complicated, ended up becoming a New York Times bestseller before getting turned into a children's animated series whose rights got acquired by Hulu, other endeavors such as a Bravo reality show called Start‐ups: Silicon Valley were short‐lived.
Regardless, Randi was having fun, this time with building her own company and not someone else's. A day after she found out that she was pregnant with her second child, the last thing Randi was expecting was to receive the call of her long forgotten teenage dreams. It was the Broadway musical Rock of Ages
